Original title: Pyrrolidine nucleotides conformationally constrained via hydrogen bonding
Authors: Pohl, Radek ; Poštová Slavětínská, Lenka ; Rejman, Dominik
Document type: Papers
Conference/Event: Symposium on Chemistry of Nucleic Acid Components /16./, Český Krumlov (CZ), 2014-06-08 / 2014-06-13
Year: 2014
Language: eng
Abstract: Conformation of pyrroPME nucleotide analogues was studied by means of NMR at different pD values in D2O solutions. Surprisingly, two stable conformers were found at pD > 9 for both cis and trans configurations and their ratio depended on the acid-base properties of nucleobase attached to pyrrolidine ring. The results of conformational analysis suggest that the conformation of the pyrrolidine ring is locked via intramolecular hydrogen bond between negatively charged phosphonate oxygen atom and protonized pyrrolidine nitrogen.
Keywords: hydrogen bond; PMEA; pyrrolidine nucleotides
Project no.: GA13-24880S (CEP)
Funding provider: GA ČR
Host item entry: Chemistry of Nucleic Acid Components. 16th Symposium, ISBN 978-80-86241-50-0

Institution: Institute of Organic Chemistry and Biochemistry AS ČR (web)
Document availability information: Fulltext is available at the institute of the Academy of Sciences.
Original record: http://hdl.handle.net/11104/0234443

Permalink: http://www.nusl.cz/ntk/nusl-174772


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